My home has always been in Boston, but I think my heart belongs in Chicago. I remember watching Ferris Bueller for the first time when I was 14 and immediately becoming fascinated by the city. I didn’t travel much growing up and didn’t make it to Chicago until I was 30, but I’ve been in love ever since! It’s clean, easy to navigate, friendly without being overbearing, and has endless possibilities for adventure. Chicago gets a bad name in the news, and while I understand that there are real problems, I personally feel safer there than at home. Chicago doesn’t have the pervasive anger and hostility that Boston has. I’ve struck up conversations with people of various backgrounds and walks of life in Chicago, and am always impressed by how interested, pleasant, and welcoming they are. I’ve now visited three times as there are always direct flights to and from Boston and Chicago. I’ve stayed just a day or so each visit, so I try to maximize my time by planning what I want to see ahead of time. Here are three sights that are a little obvious, but definitely worth seeing during a couple days in Chicago.
This is a really obvious sight, but I really think the views are worth it. It’s one of those things that you have to do at least once. Skydeck is located on the 103th floor of the Sears Tower (not Willis!), offering breathtaking 360-degree views. There’s a balcony area called The Ledge, which is completely transparent and makes you feel like you’re floating midair.
I was really glad that I bought a ticket online ahead of time when I saw the admissions line. I’m the most impatient person that ever lived, so I upgraded to the Fast Pass, which is $49. It’s a lot, but I realized it was worth it to expedite my entrance (and I even had to wait in the little line with my Fast Pass). If you’re going to be in Chicago for a few days, another great option is the CityPASS, which is $109. The CityPASS includes the Skydeck Fast Pass, along with priority entry to four other must-see stops (I actually wish I had gotten the CityPASS, maybe on my next trip!)
On my first trip to Chicago, I realized I had a couple hours to spare, so I dashed over to the Art Institute. I actually ran through the museum, trying to find the best-known pieces (using the famous Ferris Bueller scene as a guide!) I managed to see my top choices, and have been back two more times since. My favorite pieces are “A Sunday Afternoon on the Island of La Grande Jatte”, “Paris Street; Rainy Day”, “American Windows”, “Nighthawks”, and “The Old Guitarist”. Fun fact: Picasso reused a canvas to paint “The Old Guitarist”, and you can see a woman’s face underneath the neck of the guitarist. I overheard someone say this the last time I visited and was fascinated.
The museum is huge, so the ideal time allotment would be about three hours. I could spend an entire day just wandering around, intentionally getting lost inside. I first visited on a beautiful August afternoon, so there was barely a line. The second time, however, was a rainy March day, and the line looped outside. Luckily I bought a ticket online ahead of time, so I was able to waltz right inside. As I said, lines drive me insane, so I got the Fast Pass, which is $29. It allows you to bypass the general admissions line, so it was worthwhile to me. The Fast Pass is also part of the CityPASS deal!
Seadog Lakefront Speedboat Tour
The third “sight” is more of an activity, but I still wanted to include it. The Speedboat Tour is the perfect way to cool off on a balmy summer afternoon. It starts and ends at the Navy Pier, and is about 30 minutes long. I’ve gone twice because the views you get of Chicago’s skyline really can’t be beat. The tour guides are really personable too. They slow the boat periodically and share facts about the Lakefront, but not excessively. I’d say most of the ride is cruising around with music playing. The boat goes fairly fast, but not enough to really get you wet. I want to try the Extreme Thrill Ride, but I’m afraid of drowning my phone and being 1000 miles from home without one!
I’ve bought tickets online for the Speedboat tour both times, but it’s probably not necessary. I saw plenty people buying them at the dock. The tour runs about every 45 minutes during the summer months, so it’s not too bad if you miss your first choice of time. There’s plenty of food (and drink) options at the Navy Pier while you wait!
